The number of contact lens wearers worldwide has remained relatively stable over the past decade, despite the investment that has gone into contact lens technology. This is largely because 10%–50% of wearers dropout of contact lens wear within 3 years of commencement; the most common reason cited being contact lens discomfort (CLD). Of the symptoms reported, sensation of dry eye is the most common. Given the outcome of reduced wearing time, increased chair time, and ultimate contact lens discontinuation, the challenge is to identify the warning signs of CLD early on. Clinically detectable changes such as conjunctival staining, conjunctival indentation, conjunctival epithelial flap formation, lid wiper epitheliopathy, Demodex blepharitis, and meibomian gland dysfunction have been linked to CLD, highlighting the need to perform regular aftercare visits to identify these changes. At a cellular level, conjunctival metaplasia and reduced goblet cell density have been linked to CLD, leading to a downstream effect on the tear film breakup time of contact lens wearers. These factors suggest a strong link between CLD and friction, raising the need to target this as a means of minimizing CLD. The purpose of this review is to identify the clinical signs that relate to CLD as a means of earlier detection and management in order to combat contact lens dropout.